Aniline → 2-Chloro-4-phenyl-amino-quinazoline

HRID 479270Notes

Reaction equation

HRID 479270 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C([N:16](CC)C(C)C)(C)C.N[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(O)(C)C>[Cl:1][C:2]1[N:11]=[C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[NH2:16])[N:3]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 2528862,4-Dichloroquinazoline

Product 1

HCID 226398082-Chloro-4-phenyl-amino-quinazoline

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 2,4-dichloro-quinazoline (15 g), N,N-diisopropyl-ethylamine (24.9 ml) and aniline (7.5 ml) in isopropanol (75 ml) is heated to reflux for 45 min. The cold reaction mixture is filtered and the filtrate is concentrated in vacuo. The residue is crystallized from diethylether-toluene (1:1) to give 2-chloro-4-phenyl-amino-quinazoline, m.p. 194-196° C.

Workup

  1. temperatureto reflux for 45 min
  2. customThe cold reaction mixture
  3. filtrationis filtered
  4. concentrationthe filtrate is concentrated in vacuo
  5. customThe residue is crystallized from diethylether-toluene (1:1)

Sources & evidence

ORD record
ord-c45cc5dbd5a34a0dbf50012c51506115
Source dataset
uspto-grants-2003_11
Patent number
US06645774B1

Reaction notes

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